Hyperconjugation is the source of helicity in perfluorinated n-alkanes

Rodrigo A. Cormanich, David O'Hagan, Michael Buehl*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)
4 Downloads (Pure)

Abstract

Hyperconjugative, steric and electrostatic effects were evaluated as possible sources of the helicity in linear perfluorinated alkanes through analysis of natural bond orbitals and classical electrostatics. Contrary to previous rationalisations, which indicate dominating steric or electrostatic effects, this analysis indicates that hyperconjugative stabilisation through σCC-> σ*CF interactions are the underlying driving force for the origin of the observed helicity in perfluoroalkanes
Original languageEnglish
Pages (from-to)7867-7870
Number of pages4
JournalAngewandte Chemie International Edition
Volume56
Issue number27
Early online date31 May 2017
DOIs
Publication statusPublished - 21 Jun 2017

Keywords

  • Conformational analysis
  • Density-functional calculations
  • Fluorocarbons
  • Helical structures
  • Hyperconjugation

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